The Dancing Rooster: 2 Blocks from Duval in Old Town.

Key West, Florida
$533 avg/night
Bed 3

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 6

Max Sleeps

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Two of the Queen bedrooms share an en-suite bath easily assessable from either bedroom. It features a very large walk-in shower. The 3rd bedroom features a full sized bed, walk in shower and private entrance. The quaint living room has a new L Shaped Sofa that provides plenty of additional sitting room for kicking back and chill time.

Each bedroom and the living room are equipped with brand new HIDEF Samsung 4K Smart TV’s. In addition, we have recently upgraded the cottage to include FREE 300 Mbps ATT Hi Speed Business Internet, new orthopedic mattresses, and cozy linens – towels to make your stay relaxed and pleasant. There is also a brand new Central Air Conditioning system to help keep you comfortable and snug, especially during the warmer summer months!

Adjacent is a completely equipped kitchen that has granite counter tops, glass cooktop stove, microwave and refrigerator. Even wine and champagne glasses are included! A bicycle lock-up in the courtyard is available.

Blocks from the marina district, and an easy walk (.7 miles) to Ft. Zachary Taylor where Australian Pines tower over the beach. There is on street parking available (Hemmingway House .28 miles, Duval Street 1 block, Marina District 7 blocks, beach .7 miles).

There is a health food store located directly across the street called 'The Sugar Apple' which serves fresh fruit smoothies, lunch, and offers a variety of health food. A CVS is located one block away. A bike and scooter rental location is one block away.

A 3-night minimum stay required and strict No Smoking policy applies. Please contact owner for exception to 3 night minimum

Please note rates are subject to change and are higher during Event Periods such as Fantasy Fest, Gay Pride, Memorial Day, Christmas Week, New Year's Week, Thanksgiving, etc. Longer stays than 3 days may be required during event periods.

NOTE: There is No Dedicated Parking included with this rental. Directly on Simonton Street are (4) spaces and available on first come basis. We do recommend keeping the car parked and walk, bike or use the bus service, The Duval Loop. The Duval Loop provides FREE Hop on, Hop off bus service, operates every day, and stops a half block from the cottage. https://www.cityofkeywest-fl.gov/326/Duval-Loop

IMPORTANT: We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related issues, or other unexpected circumstances. While travel insurance can be purchased during the booking process, you may want to consider other reputable travel insurance providers, such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway and Red Sky. We encourage you to review their coverage options and rates to find the best fit for your needs.

For those traveling during Florida's hurricane season (June 1 – November 30), travel insurance is especially important. Please note that NO refunds will be issued for weather-related disruptions or early departures.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 20 Lbs Per Pet) Pet Friendly Service Animals Exempt From Fees Welcoming Dogs Only
  • BEACH

    Near The Beach
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 750 Sq Ft (70 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Ice Maker Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • OUTDOORS

    Barbecue Grill Fenced Yard Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Fitness Facilities Nearby Kayaking Nearby Parasailing Nearby Power Boating Nearby Sailing Nearby Scuba Diving Nearby Wildlife And Game Walks Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Children's Dinnerware
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    No Elevators Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Submitted Jul 16, 2021

    Stayed Jul 12, 2021

    Comfortable, equipped with all basic needs, could have had a few notes on location of grocery store etc. that could have speeded up our settling in. Manager was helpful and available if needed. Great location , not too far or too close to local attractions and tour trolleys etc that allowed some quiet rest time when needed. We would re book should we visit again.

  • E A M.

    Submitted Apr 1, 2026

    Stayed Mar 27, 2026

    Super clean, responsive property manager and great location near Duval Street.

  • Rhonda B.

    Submitted Mar 26, 2026

    Stayed Mar 22, 2026

    Great location. Just as advertised.They went out of there way to allow us to check in early and the property manager was great. Would definitely stay here again.

  • Katharine L.

    Submitted Mar 9, 2026

    Stayed Mar 4, 2026

    The location is perfect. Easy walk to Duval and other places. Quiet, quaint neighborhood.

  • Mercedes A.

    Submitted Mar 6, 2026

    Stayed Feb 26, 2026

    Such a great stay. A nice walk to duval for nightlife!

  • Angela F.

    Submitted Feb 24, 2026

    Stayed Feb 7, 2026

    Great location cleaning service was super nice was able to leave luggage at house before check in time plane arrived early so we didnt have to carry luggage around answer to question was prompt only thing waa shower heaad in one bathroom would not stay up and shows they have a grill on site but that has not yet been replaced everything else was great

  • michael k.

    Submitted Jan 19, 2026

    Stayed Jan 14, 2026

    Great place, great location! Worked out perfect!

  • Jason S.

    Submitted Jan 13, 2026

    Stayed Jan 5, 2026

    Responsive host & property manager. Great location within walking distance to shops, restaurants, & attractions. Property was clean & beds comfortable, but would recommend having spare blankets should anyone want to sleep on the sofa. Would definitely stay there agsin.

  • Mike B.

    Submitted Jan 9, 2026

    Stayed Dec 27, 2025

    Location is the strongest selling point for sure. The unit is small but makes the most of its space.

  • Sherry H.

    Submitted Dec 22, 2025

    Stayed Dec 16, 2025

    Beautiful bungalow. Clean and has everything you need. Comfortable and located walkable distance to all attractions on the island. Nice neighborhood! Enjoyed our stay and plan to return!

  • Tammra B.

    Submitted Dec 16, 2025

    Stayed Dec 11, 2025

    Had a lovely visit. The cottage was lovely and great location. Had a minor issue (co2 detector) and the property manager was quick to take care of it for us so we could go on with our day. Turned out it just needed to be changed and really didn’t matter much because every room had a detector. Would highly recommend!!

  • Greg S.

    Submitted Dec 11, 2025

    Stayed Dec 4, 2025

    Excellent location. Wrought can walk to just about anywhere you want to on the island. 4 of us stayed in the 3 BR house. 6 people would have been a very tight fit. Bedrooms are small. Tight fit for 2 suitcases. Beds were soft. Pillow's were flat. 2 ice trays in small freezer, so go to CVS down the street to purchase ice. 1bath towel per person for our 6 day stay, which was inadequate in this tropical environment. Both bathrooms ran out of toilet paper. We all really enjoyed being able to sit outside on the front patio. There was room for all 4 of us.

  • Christina C.

    Submitted Dec 6, 2025

    Stayed Nov 29, 2025

    The property was exactly as described. It was clean, comfortable, and spacious for our party of 4. Communication was friendly and expedient. Check in was simple. Location, location, location! We were within walking distance to so much and rented a golf cart for anything further away. I would definitely book again! Thank you…10/10!

  • Bob C.

    Submitted Nov 13, 2025

    Stayed Nov 5, 2025

    Beautiful home , that was perfect for our family of 5! Loved the double door accessibility. Very accommodating!

  • John P.

    Submitted Oct 16, 2025

    Stayed Oct 9, 2025

    Great communication. Clean property. Easy to walk to most things.

  • Kristi

    Submitted Oct 9, 2025

    Stayed Oct 2, 2025

    What a perfect location in Olde Town Key West! We walked to many nice places and, if it was a bit further, a very reasonable taxi took us there. Our favorite part was sitting on the front porch and just watching the town people go by! The awning was the icing on the cake as it created the perfect shade to sit and enjoy! Inside was ample room, nice kitchen and BIG TV’s! We will certainly book here again for our next Keys trip.

  • John B.

    Submitted Oct 4, 2025

    Stayed Sep 28, 2025

    Loved it!!

  • Melissa F.

    Submitted Oct 1, 2025

    Stayed Sep 25, 2025

    Everything was walkable. Loved the front porch

  • Kimberly O.

    Submitted Sep 24, 2025

    Stayed Sep 18, 2025

    We had a really nice stay. Property Manager was wonderful and receptive. No issues at all. Would definitely recommend.

  • JEFFREY Z.

    Submitted Aug 13, 2025

    Stayed Jul 26, 2025

    Great place to stay

  • Matthew C.

    Submitted Jun 20, 2025

    Stayed Jun 15, 2025

    Great time. Would stay again.

  • Dave S.

    Submitted May 13, 2025

    Stayed May 9, 2025

    The property owner and staff do a great job of communicating. House is very clean and worked well for us

  • Tracy S.

    Submitted May 11, 2025

    Stayed May 5, 2025

    The home looks just like the pictures and was very comfortable. It was a very quick walk to Duval Street which we loved. We would stay here again!

  • Carol M.

    Submitted Apr 24, 2025

    Stayed Apr 20, 2025

    The house was perfect for our group of 3 couples- we loved sitting out on the front porch - got lucky and parked golf cart in front every evening- close to Duval St - quiet area

  • Suzanne D.

    Submitted Mar 30, 2025

    Stayed Mar 27, 2025

    Clean, perfect location in Old Town Key West. The property manager was so accommodating and quickly got back to me with answers to my questions. Would definitely stay there again.

  • Submitted Mar 17, 2025

    Stayed Mar 9, 2025

    This location is great - easy to get to bight and Duval St. The interior was very clean. Good shower, good room lay out, good mattress. Like the two different entrances as I stayed with my sister's family which gave us privacy. Good prompt response from owner and staff.

  • Cecile S.

    Submitted Mar 10, 2025

    Stayed Mar 3, 2025

    The Dancing Rooster has a fantastic location. We walked everywhere! It was very clean and had everything we needed for a little cooking. We very much enjoyed our stay.

  • Gerrilynne S.

    Submitted Feb 14, 2025

    Stayed Feb 7, 2025

    Great location

  • Kevin C.

    Submitted Feb 7, 2025

    Stayed Feb 1, 2025

    Fantastic week, bungalow was the perfect location to enjoy everything Key West has to offer. Spent late evenings on the patio playing games and speaking with passerby’s.

  • lauashhei

    Submitted Jan 24, 2025

    Stayed Jan 10, 2025

    It was really important for my group to be able to walk to the majority of the food and things. It was a great spot to do that from. Our only regret is we did not come during a time of year when the weather was touch warmer.

  • Brett M.

    Submitted Jan 21, 2025

    Stayed Jan 6, 2025

    The property was clean and functional. It was conveniently located just 1 block from Duval. 6 of us stayed 4 nights. Kitchen was small but worked for us. We had breakfast and lunches, plus 1 family dinner where we used the BBQ grill. Very satisfied and would stay again. it wasn't problem for us but you had to go through bedroom2 to get to bedroom 3 from the interior. Bedroom 3 also had its own exterior door to allow you to exit and re-enter via main door to avoid passing through BR#2.

  • David K R.

    Submitted Jan 21, 2025

    Stayed Jan 13, 2025

    3 relaxing days

  • Maureen M.

    Submitted Dec 2, 2024

    Stayed Nov 28, 2024

    Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St.

  • Keith P.

    Submitted Nov 28, 2024

    Stayed Nov 25, 2024

    Comfy beds, clean sheets. Parking was as described. No spot the first night and had to move the car the next morning. Nice central location just off Duval.

  • Leann L.

    Submitted Nov 1, 2024

    Stayed Oct 28, 2024

    Key West after fantasy week we had a great time manager always got right back to us

  • Austin D.

    Submitted Aug 16, 2024

    Stayed Aug 10, 2024

    The location of this property is unbeatable! Very close to Duval street with plenty of restaurants and shopping nearby. The home was clean and well kept up also. Property manager was very quick to respond and helpful!

  • Bea C.

    Submitted Aug 11, 2024

    Stayed Jul 28, 2024

    Biggest frustration was parking. There were no spots available near the unit until later in the evening. We had to unload across the street and then relocate the vehicle to a legal parking spot. Once you find parking, stay there and walk or Uber during the day. Typical Key West drama. The unit was comfortable, but the kitchen was barely adequate. Don’t plan on preparing any family meals and it’s fine.

  • Amber W.

    Submitted Aug 9, 2024

    Stayed Jul 19, 2024

    We chose to spend my husband and daughter’s birthday in the Keys this year. The property is located in walking distance of everything and if you’re tired of walking, a scooter/golf cart business is right on the corner! The property was extremely clean and had all the amenities to make vacation easier. We utilized the grill and kitchen daily! If you’re like me and love to boil your skin in the shower, this place has the best hot water for showers! The owner and property manager are lovely and easy to communicate with. I highly recommend this property and will personally book with them again in the future!

  • Adam H.

    Submitted Jul 29, 2024

    Stayed Jul 25, 2024

    We had a great stay and wonderful trip to Key West. The location is great for walking and Nancy the property manager was great and very helpful in anything we asked.

Your dates are Available!

Total

Includes taxes and fees
$629+
View details